hair care compositions containing one or more quaternary nitrogen derivatives of trialkylamino hydroxy organosilicon compounds have superior conditioning capability for hair.
|
10. An aqueous hair conditioning shampoo composition comprising:
(A) From about 0.1 to about 10.0 weight percent of at least one compound of the formula: ##STR19## wherein: R is a monovalent hydrocarbon radical having from 1 to 18 carbon atoms; R' is a divalent alkylene radical having from 1 to 18 carbon atoms or a divalent hydrocarbonoxy radical having from 1 to 18 carbon atoms wherein the oxygen in said hydrocarbonoxy radical is present in the form of ether linkages, and wherein the hydrocarbon portion of said hydrocarbonoxy radical is present in the form of divalent alkylene radicals; X- is halide anion; x has an average value of from about 2 to 20; and y has an average value of from about 20 to 200; (B) From about 75 to about 99.9 weight percent water; and (C) From about 9 to about 30 weight percent of one or more amphoteric, cationic, anionic, non-ionic, polar non-ionic or zwitterionic surfactants.
1. A method of conditioning hair which comprises applying to said hair an effective amount of a composition containing:
(A) From about 0.1 to about 10.0 weight percent of at least one compound of the formula: ##STR17## wherein: R is a monovalent hydrocarbon radical having from 1 to 18 carbon atoms; R' is a divalent alkylene radical having 1 to 18 carbon atoms or a divalent hydrocarbonoxy radical having from 1 to 18 carbon atoms wherein the oxygen in said hydrocarbonoxy radical is in the form of an ether linkage and wherein the hydrocarbon portion of said hydrocarbonoxy radical is present in the form of divalent alkylene radicals; X- is halide anion; x has an average value of from 2 to 20; and y has an average value of from 20 to 200; (B) From about 75 to about 99.9 percent water; and (C) From about 0 to about 30 weight percent of one or more amphoteric, cationic, anionic, non-ionic, polar non-ionic or zwitterionic surfactants.
2. A method according to
3. A method according to
5. A method according to
--C3 H6 OCH2 --. 6. A method according to
7. A method according to
8. A method according to
9. A method according to
12. An aqueous shampoo composition according to
15. An aqueous shampoo composition according to
|
This invention relates to hair care compositions. More particularly, this invention relates to hair conditioning compositions which are especially useful for conditioning hair by leaving it in a pleasing and satisfactory, soft, lustrous and easily manageable condition. In a more specific aspect, this invention relates to aqueous, homogenous and conditioning shampoo compositions which exhibit outstanding cleaning characteristics, as well as being characterized by an outstanding capacity for conditioning cleaned hair.
It is well known that simple aqueous detergent compositions are useful for the cleansing of hair by promoting the removal of soil and excess natural oil. For practical use shampoo compositions must not dull the hair by removing all of the natural oils from the hair nor damage it by harsh detergent action. In addition, it must provide lather in both hard and soft water and be sufficiently stable so that it does not deteriorate on standing or in the course of normal use. In most detergent compositions now in use the removal of natural oils to a greater or lesser extent is unavoidable as a part of the cleansing action, as is some hair damage as a result of the action of detergent. Furthermore, shampoo compositions which thoroughly clean the hair usually leave it in a statically electrified state, in which the individual hairs repel each other, or in a state in which simple combing produces this undesired electrification. In either case, the hair is very difficult to manage. To overcome these defects, chemists in the field of hair treatment have vigorously explored alternative or complementary shampoo and hair conditioning systems. For example, in many conventional shampoo compositions, it is customary to include an additive such as a lanolin derivative, glycol, fatty esters or protein in an effort to condition the hair by replacing the stripped oils so as to leave the hair more manageable and natural after shampooing. Unfortunately, when these derivatives are incorporated directly into a shampoo, they may cause a loss of sudsing, sheen, and leave the hair with a sticky and unnatural feeling. Alternatively, a variety of products such as cream rinses, conditioners, weave sets and hair sprays, containing antistatic agents, conditioning agents and the like, have been developed for use after shampooing to counteract the adverse effects of shampooing on the hair and to return its sheen, combability and wave set retention and to reduce flyaway hair. It is obvious that the use of these additional materials is naturally necessarily expensive and requires additional time and effort involving additional application and treatment of the hair on the part of the users.
It is an object of this invention to provide a hair conditioning composition which may be used subsequent to shampooing or, alternatively, may be used in conjunction with a detergent in a shampoo composition.
It is an additional object of this invention to provide a stable conditioning shampoo composition to be used without a subsequent conditioning treatment.
It is further an object of this invention to provide a conditioning shampoo composition which exhibits excellent cleansing and lathering properties along with excellent conditioning properties to impart sheen, manageability and wave set retention to the cleansed hair.
It is another object of this invention to provide a post-shampooing composition which conditions hair by leaving it in a pleasing and satisfactory, soft, lustrous and easily manageable condition.
Other objects and advantages will become readily apparent from the following description and appended claims.
We have now discovered that compositions containing one or more quaternary nitrogen derivatives of trialkylamino hydroxy organosilicon compounds exhibit superior conditioning capability for the hair. The compositions of this invention leave the hair lustrous and pleasant to the touch. These compositions also reduce or entirely eliminate the snarling of wet hair which ordinarily results as the users fingers become entangled with the hair during the shampooing process. In addition, the compositions of the present invention promotes easy wet combing of the washed and rinsed hair, so that the hair shafts slip easily on each other and past the comb. They also promote easy dry combing and the reduction of static electrification of the hair. Thus, there is minimal drag on the comb and the strands of hair do not tend to fly away and become disaligned as a result of the dry combing process.
The aqueous hair conditioning compositions of this invention comprise:
A. From about 0.1 to about 10.0 weight percent of a quaternary nitrogen derivative of a trialkylamino hydroxy organosilicon compound; and
B. From about 75 to about 99.9 weight percent water.
C. From about 0 to about 30 weight percent of one or more surfactants selected from the group consisting of amphoteric, polar non-ionic, anionic, cationic, non-ionic, zwitterionic surfactants or a combination thereof.
All weight percents are based on the total weight of the composition. As optional ingredients, the composition may also include other conditioning agents known to those of skill in the art.
The essential components of the conditioning composition of this invention are quaternary nitrogen derivatives of trialkylamino hydroxy organosilicon compounds which corresponds to the formula: ##STR1## wherein: R is a monovalent hydrocarbon radical having from 1 to 18 carbon atoms;
R' is a divalent hydrocarbon radical having from 1 to 18 carbon atoms as a divalent hydrocarbonoxy radical having from 1 to 18 carbon atoms wherein the oxygen of said hydrocarbonoxy radical is in the form of an ether linkage.
X- is halide anion;
x has an average value of from 2 to 20;
y has an average value of from 20 to 200.
It should be observed in the above generic formula that various R groups need not be identical. The structural representation is intended to show each individual R' group may be the same or different.
Suitable monovalent hydrocarbon groups represented by R in the structural representation set forth hereinabove include alkyl, alkenyl, aryl, alkaryl, aralkyl or like groups. Illustrative of more specific R groups or methyl, ethyl, propyl, butyl, isobutyl, decyl, octadecyl, cyclopentyl, cyclohexyl, naphthyl, vinyl, butenyl, cyclohexenyl, tolyl, xylyl, benzyl, and betaphenylethyl.
Suitable divalent hydrocarbon groups which are represented by R are alkylene, arylene or aralkylene radicals. Suitable divalent hydrocarbonoxy radicals represented by R' are the same as the permissible hydrocarbon radicals except that they contain one or more ether linkage, that is a functional unit of the formula, --CH2 OCH2 --. Illustrative of R' groups are methylene, ethylene, propylene, butylene, phenylene, phenylmethylene, methylphenylene or any of the aforementioned groups having one or more ether linkages incorporated within the basic structure.
The preferred and particularly efficacious quaternary trialkylamino hydroxy organosilicon derivatives for use in the compositions of this invention are those of the formula: ##STR2## wherein: R' is divalent alkylene having from 1 to 8 carbon atoms;
x has an average value of from 2 to 8;
y has an average value of from 20 to 50.
The quaternary trialkylamino hydroxy organosilicon derivatives employed in the compositions of this invention are known compounds that can be prepared by known methods known to those skilled in the art. For example, these compounds can be conveniently prepared by the method disclosed in U.S. Pat. No. 3,389,160.
The composition of this invention may also include as an optional ingredient from 9 to about 30 weight percent of one or more surfactants, i.e. detergents, selected from the group consisting of amphoteric anionic, cationic, polar non-ionic, non-ionic, zwitterionic surfactants or a mixture thereof to form a shampoo composition. Amphoteric, polar non-ionic, non-ionic and zwitterionic surfactants are prepferred for use in the composition of this invention. This surfactant functions as a lathering and cleansing agent.
By polar non-ionic detergent is meant a detergent in which the hydrophilic group contains a semi-polar bond directly between two atoms, e.g. N→O, P→O, As→O, and S→O. There is charge separation between the two directly bonded atoms, but the detergent molecule bears no net charge and does not dissociate into ions at neutral pH.
The polar non-ionic detergents which can be used in conjunction with or as an alternative to the amphoteric detergent includes open-chain aliphatic amine oxides of the general formula R1 R2 R3 N→O. The arrow is a conventional representation of a semi-polar bond. These compounds are generally prepared by the direct oxidation of the appropriate tertiary amine. When R1 is a much longer chain than R2 and R3, the amine oxides have surface activity. For the purpose of this invention, R1 is an alkyl, alkenyl or monohydroxyalkyl radical having from about 10 to about 16 carbon atoms. Desirable surface active properties are lost if R1 is substantially less than about 10 carbon atoms and the compounds are insufficiently soluble if R1 is greater than about 16 carbon atoms, R2 and R3 are each selected from the group consisting of methyl, ethyl, propyl, ethanol and propanol radicals. Preferably R1 is a dodecyl radical or a mixture of dodecyl with decyl, tetradecyl and hexadecyl such that at least 50% of the radicals are dodecyl radicals. R2 and R3 are preferably methyl radicals. A preferred amine oxide for the purpose of this invention is a dodecyldimethylamine oxide.
Other operable polar non-ionic detergents are the open chain aliphatic phosphine oxides having the general formula R1 R2 R3 P→O, wherein R is an alkyl, alkenyl or monohydroxyalkyl radical ranging in chain length from 10 to 18 carbon atoms, and R2 and R3 are each alkyl and monohydroxy-alkyl radicals containing from 1 to 3 carbon atoms. A preferred phosphine oxide is dodecyldimethyl phosphine oxides which together with a method of preparation is fully described by Yoke et al. in application Ser. No. 173,834, filed Feb. 16, 1952, now U.S. Pat. No. 3,304,330.
As hereinbefore stated, amphoteric detergents can be used in conjunction with or in place of the polar non-ionic detergents described above. As used herein, the term "amphoteric" is interchangeable with the term "ampholytic". Amphoteric detergents are well known in the art and many operable detergents of this class are disclosed by A. M. Schwartz, J. W. Perry and J. Birch in "Surface Active Agents and Detergents," Interscience Publishers, New York 1958, Vol. 2. Examples of suitable amphoteric detergents include, for example, alkyl betaiminodipropionates, RN(C2 H4 COOM)2 ; alkyl beta-amino propionates, RN(H)C2 H4 COOM; and long chain imidazole derivatives having the general formula: ##STR3##
In each of the above formulae R is an acyclic hydrophobic group containing from about 8 to about 18 carbon atoms; G is - OH or other anion or an acid salt or the salt of an anionic surface active sulfate or sulfonate and M is a cation to neutralize the charge of the anion. Specific operable amphoteric detergents include the disodium salt of lauroylcycloimidinium-1-ethoxyethionic acid-2-ethionic acid, dodecyl beta alanine, and the inner salt of 2-trimethylamino lauric acid. The substituted betaines and sultaines, such as alkyl ammonio acetates wherein the alkyl radical contains from about 12 to 18 carbon atoms can also be used. The betaine and sultaine types of ampholytic detergents are zwitterionic quaternary ammonium compounds having a general formula: ##STR4## wherein R1 is an alkyl having from about 10 to about 18 carbon atoms, R2 and R3 are each alkyl having from about 1 to about 3 carbon atoms, R4 is an alkylene or hydroxyalkylene having from 1 to 4 carbon atoms, and X is an anion selected from the group consisting of --SO3- and --COO-.
Compounds which conform to the above general formula are characterized by the presence of both positive and negative charges which are internally neutralized (i.e. zwitterionic). When the anion X is --SO3-, these compounds are referred to as "sultaines." The term "betaines" is employed when the anion X is --COO-. The following structural formulae are illustrative of the two types and their inner salt character. ##STR5##
When one R in the above formulae is a high weight alkyl having from about 10 to 18 carbon atoms, these compounds are surface active and have good detergency powers. If the high molecular weight alkyl contains less than about 10 carbon atoms, surface activity and detergency are inadequate. If this group contains more than about 18 carbon atoms, the compounds are not sufficiently soluble to be of utility in this invention. Preferably, the high molecular alkyl will contain from 12 to 16 carbon atoms or a mixture of dodecyl with decyl, tetradecyl, and hexadecyl radicals. A convenient source of a suitable mixture of alkyl groups is the middle cut of coconut fatty alcohol which has the approximate chain length composition: 2%-C10, 66%-C12, 23%-C14, and 9%-C16. Particular advantage can be gained by employing betaine or sultaines having an alkyl containing 16 carbon atoms in the compositions of this invention. The alkyl can, of course, contain one or more intermediate linkages such as ether or polyether linkages or non-functional substituents such as hydroxyl or halogen which do not substantially affect the hydrophobic character of the group.
Preferred compounds which fall within the above class include -1-(alkyldimethylammonio)acetate, 1-(alkyldimethylammonio)propane-3-sulfonate and 1-(alkyldimethylammonio)-2-hydroxy-propane-3-sulfonate wherein the alkyl contains from 12 to 16 carbon atoms.
The organic anionic detergent composition which may be included in the compositions of this invention may be either a water-soluble soap or a non-soap synthetic detergent or a mixture thereof.
Operable non-soap anionic organic detergents include, for example, water-soluble salts of organic sulfuric reaction products having in their molecular structure an alkyl group containing from about 8 to 20 carbon atoms and a radical selected from the group consisting of sulfuric acid ester and sulfonic acid radicals. Important examples of this type of non-soap anionic synthetic detergent, include the sodium or potassium alkyl sulfates, especially those derived by sulfation of higher alcohols produced by reduction of tallow of coconut oil glycerides; sodium or potassium alkyl benzene sulfonates, especially those of the types described by Guenther et al. in U.S. Pat. No. 2,220,099, granted Nov. 5, 1940, and by Lewis in U.S. Pat. No. 2,477,383, granted July 26, 1949, in which the alkyl group contains from about 9 to about 15 carbon atoms; sodium alkylglyceryl ether sulfonates, especially those ethers of higher alcohols obtained from tallow and coconut oil; sodium coconut oil fatty acid monoglyceride sulfates and sulfonates; sodium salts of sulfuric acid esters of the reaction product of one mole of a higher fatty alcohol (i.e. tallow or coconut oil alcohols) and about 3 moles of ethylene oxide; and others well known in the art, a number being specifically set forth in Byerly, U.S. Pat. Nos. 2,486,921 and 2,486,922.
Additional non-soap anionic organic synthetic detergents which can be used in this invention include the salts of the condensation products of fatty acids with sarcosine, i.e., acyl sarcosinate, wherein the acyl radical has a chain length range from about 10 to 18 carbon atoms. An especially preferred acyl sarcosinate for the purpose of this invention is sodium lauroyl sarcosinate.
Preferably, the non-soap anionic organic detergent will be of the high sudsing type as for example the alkylglyceryl-ether sulfonates, the sulfated fatty alcohols or the alkyl ether ethylene oxide sulfates wherein the ethylene oxide chain averages 3 units, and acyl sarcosinates, all as more fully set forth above. These and the foregoing detergents can be used in the form of their sodium, potassium or lower alkanolamine such as triethanolamine salts.
Conventional soaps may also be used as the anionic detergent component of this invention. Suitable soaps include the sodium, potassium, and lower alkanolamine salts of higher fatty acids of naturally occurring vegetable or animal fats and oils. For example, sodium, potassium and triethanolamine salts of fatty acids occurring in coconut oil, soybean oils, castor oil, tallow or synthetically produced fatty acids may be used.
Coconut, lauric and myristic mono- and diethanolamides may be used up to about 8% of the formula weight. The compounds serve to aid in the form stabilization of the polymer-detergent composition; however, they are not essential. Small quantities, up to about 5%, of non-ionic surfactants such as ethoxylated higher alcohols, alkyl phenols, and fatty acids may also be included as compatability agents and to promote rinsing.
The pH of the conditioning compositions of this invention may range from a pH of about 5.0 to a pH of about 8∅ Higher and lower pH values are undesirable because of their harsh properties which are detrimental to the hair and to their relative toxicity. The preferred formulations of this invention have a neutral pH of 7. Adjustment of the pH may be accomplished by the addition of non-toxic inorganic and organic acids, such as citric acid or phosphoric acid and bases such as triethanolamine and sodium or potassium hydroxide.
In addition to the essential ingredient, the compositions of this invention may include minor quantities of optional materials which are added for various specific purposes. Such other ingredients include, but are not limited to, medicaments, solvents, thickeners, perfumes, bactericides, sequestering agents, foam stabilizers, and opacifier, all of which are commonly used and are well known to be capable of use in hair care formulations. The compositions of this invention may also include other conditioning agents.
The hair conditioning compositions of this invention can be conveniently prepared by a simple blending of the ingredients in the above indicated weight percents. The order of addition is not critical and will be determined solely on the basis of convenience.
The following examples are provided to more clearly illustrate this invention. In Examples I and II:
SILICONE-I: is a compound of the formula: ##STR6##
SILICONE-II: is a compound of the formula: ##STR7##
SILICONE-III: is a compound of the formula: ##STR8##
SILICONE IV: is a compound of the formula: ##STR9##
SILICONE V: is a compound of the formula: ##STR10##
SILICONE VI: is a compound of the formula: ##STR11##
SILICONE VII: ##STR12##
SILICONE VIII: is a compound of the formula: ##STR13##
SILICONE IX: is a compound of the formula: ##STR14##
SILICONE X: is a compound of the formula: ##STR15##
SILICONE XI: is a compound of the formula: ##STR16##
A number of compositions were prepared which illustrate the wide range of compositions possible in the practice of this invention. The percent by weight compositions of these composition are set forth in Table I. The compositions of Table I are conveniently prepared by simply mixing the quaternary trialkylamino hydroxy organosilicon derivative and water until complete dispersal is achieved followed by the addition of the optional ingredients with stirring until a uniform homogeneous mixture is achieved. Acid or alkali is added immediately after the addition of the detergent for pH adjustment, as desired and as required. Perfumes, dyes and preservatives are normally added after pH adjustment.
TABLE I |
__________________________________________________________________________ |
COMPOSITIONS AND AMOUNTS BY WEIGHT PERCENT |
INGREDIENT I II III |
IV V VI VII |
VIII |
IX X XI |
__________________________________________________________________________ |
I. QUATERNARY |
HYDROXYORGANOSILICONE |
1 SILICONE I 1.5 |
-- -- -- -- -- -- -- -- -- -- |
2 SILICONE II -- 1.5 |
-- -- -- -- -- -- -- -- -- |
3 SILICONE III -- -- 1.5 |
-- -- -- -- -- -- -- -- |
4 SILICONE IV -- -- -- 1.5 |
-- -- -- -- -- -- -- |
5 SILICONE V -- -- -- -- 1.5 |
-- -- -- -- -- -- |
6 SILICONE VI -- -- -- -- -- 1.5 |
-- -- -- -- -- |
7 SILICONE VII -- -- -- -- -- -- 1.5 |
-- -- -- -- |
8 SILICONE VIII -- -- -- -- -- -- -- 1.5 |
-- -- -- |
9 SILICONE IX -- -- -- -- -- -- -- -- 1.5 |
-- -- |
10 SILICONE X -- -- -- -- -- -- -- -- -- 1.5 |
-- |
11 SILICONE XI -- -- -- -- -- -- -- -- -- -- 1.5 |
II. |
WATER 98.5 |
98.5 |
98.5 |
98.5 |
98.5 |
98.5 |
98.5 |
98.5 |
98.5 |
98.5 |
98.5 |
__________________________________________________________________________ |
Selected species of the conditioning compositions of this invention were evaluated to determine their performance in hair care applications. The compositions of this invention prepared in Example I were evaluated in creme rinse protocols, on both virgin brown hair and bleached hair. Evaluations of performance factors and test procedures were combability, fly-away, conditioning, overall feel and appearance.
Two grams, ten inch tresses were prepared from both virgin brown Italian and bleached hair. (De Meo Brothers, New York, N.Y.) Each tress was wet with tap water and two grams of the control shampoo per two grams of tress was worked thoroughly through the hair. The tresses were rinsed with 40°C tap water and the process repeated. The excess water was blotted from the tress using paper towels. One milliliter of the creme rinse lotion is applied to the hair and gently worked through the tress, taking care not to tangle or snarl the tress. The wet tresses were evaluated for feel and appearance. Using the wide tooth end of a black rubber comb, the tresses were combed. The length, in inches the comb traveled without meeting resistance was noted. This value is the wet combability. Each tress was hung individually and combed through. The procedure was carried out on three tresses. Using the wide tooth comb end, a black rubber comb was gently combed through each tress and the length, in inches, the comb travels without meeting resistance is noted. This value is the dry combability.
Each tress was vigorously combed ten times and the width of the bundle and the overall width of the fan (including single hairs) were measured in inches. These values are termed by flyaway.
TABLE II |
__________________________________________________________________________ |
PERFORMANCE ON VIRGIN BROWN HAIR |
COMPOSITION AND PERFORMANCE |
PROPERTY |
1 2 3 4 5 6 7 8 9 10 11 |
__________________________________________________________________________ |
Wet |
Combability |
3.4 6.2 6.2 4.2 4.2 3.9 6.2 4.2 4.4 5.4 3.0 |
(in.)1 |
sl. very very very very very very very very |
Wet |
Feel slippery |
slippery |
slippery |
slippery |
slippery |
slippery |
slippery |
slippery |
slippery |
slippery |
slippery |
very very |
Wet sl. good good good good good good good good good |
Appearance |
sheen |
sheen |
sheen |
sheen |
sheen |
sheen |
sheen |
sheen |
sheen |
sheen |
sheen |
Dry |
Combability2 |
1.0 0.4 1.2 1.0 1.0 0.3 1.2 0.3 1.2 0 0.3 |
very very very very |
Dry good good good good good good good good good |
Appearance |
sheen |
sheen |
sheen |
sheen |
sheen |
sheen |
sheen |
sheen |
sheen |
sheen |
sheen |
Flyaway |
(in.)3 |
-0.5 -0.2 -0.5 -0.5 0.7 0.5 -0.3 0.5 0.3 -0.3 0 |
__________________________________________________________________________ |
1 Number of inches over the control that the comb has traveled |
through wet hair. |
2 Number of inches over the control that the comb has traveled |
through dry hair. |
3 Number of inches that the flyaway has been reduced or increased |
compared to the control. |
TABLE III |
__________________________________________________________________________ |
PERFORMANCE ON BLEACHED HAIR |
COMPOSITION AND PERFORMANCE |
PROPERTY |
1 2 3 4 5 6 7 8 9 10 11 |
__________________________________________________________________________ |
Wet |
Combability |
5.8 5.5 4.5 4.5 4.5 4.5 3.5 4.5 1.2 2.2 0.8 |
(in.)1 |
Wet Feel |
raspy |
slippery |
slippery |
slippery |
slippery |
slippery |
slippery |
slippery |
slippery |
slippery |
raspy |
Wet sl. good sl. good sl. |
Appearance |
sheen |
sheen |
sheen |
sheen |
sheen |
sheen |
sheen |
slippery |
sheen |
sheen |
dull |
Dry |
Combability2 |
5.7 5.4 2.7 2.3 2.3 1.3 5.7 1.6 5.7 4.4 -0.4 |
Dry good v.good |
good good good good sl. good |
Appearance |
sheen |
sheen |
sheen |
sheen |
sheen |
sheen |
sheen |
sheen |
sheen |
sheen |
sheen |
Flyaway |
(in.)3 |
-1.1 -0.6 -1.0 -0.7 -1.2 -1.0 -0.6 -1.2 -0.8 -1.0 -0.8 |
__________________________________________________________________________ |
1 Number of inches over the control that the comb has traveled |
through wet hair. |
2 Number of inches over the control that the comb has traveled |
through dry hair. |
3 Number of inches that the flyaway has been reduced or increased |
compared to the control. |
The test results set forth in TABLES II and III illustrate the outstanding conditioning capacity of the composition of this invention in conventional application systems, shampoos, and creme rinse compositions. The tresses treated with the conditioning compositions of this invention exhibit outstanding luster and managability.
A selected specie of this invention was evaluated in comparison with a known hair conditioning agent, in order to determine hair conditioning relative efficacy. The known hair conditioning agent selected for these studies was, Stearyl Dimethyl Benzyl Ammonium Chloride, "SB-25". The quaternary trialkylaminohydroxy organosilicon compounds selected for these studies was SILICONE II. The conditioning capacities of these compositions were determined on both virgin brown and bleached hair. Each composition was evaluated in a water solution at three concentration levels, 0.5, 1.5 and 3.0 weight percent based on the total weight of the water solution. The test procedures were as described in EXAMPLE II. The results of these tests are set forth in TABLE IV hereinbelow.
TABLE IV |
__________________________________________________________________________ |
SILICONE I SB-25 |
VIRGIN BROWN HAIR |
BLEACHED HAIR |
VIRGIN BROWN HAIR |
BLEACHED HAIR |
PROPERTY 0.5% 1.5% |
3.0% |
0.5% |
1.5% |
3.0% |
0.5% 1.5% |
3.0% |
0.5% |
1.5% |
3.0% |
__________________________________________________________________________ |
Wet Combability (in.)1 |
10.00 |
10.0 |
9.7 9.3 9.7 9.7 9.5 9.3 10.0 |
7.0 8.7 5.0 |
Dry Combability (in.)2 |
10.0 10.0 |
9.7 9.7 10.0 |
10.0 |
9.0 10.0 |
10.0 |
9.3 9.7 7.3 |
Flyaway, Inches3 |
4.0 4.2 4.2 2.7 2.5 2.2 4.3 3.8 4.2 3.3 3.5 3.7 |
__________________________________________________________________________ |
1 Number of inches over the control that the comb has traveled |
through wet hair |
2 Number of inches over the control that the comb has traveled |
through dry hair |
3 Number of inches that the flyaway has been reduced or increased |
compared to the control |
The data set forth in TABLE IV illustrates the superior conditioning capacity of the compositions of this invention in comparison with known conditioning agents. For example, the performance of 0.5 weight percent of Silicone-I composition is equal to that of a 3.0 weight percent SB-25 solution on virgin brown hair in both wet combability and flyaway. On bleached hair, the SB-25 compositions failed to reach the performance level of a 0.5 weight percent Silicone I, composition regardless of the concentration level. The experimental data clearly indicates that a 0.5 weight percent SILICONE-I composition outperforms or at the least equals the performance of a 3.0 weight percent SB-25 composition. As such SILICONE-I is approximately six times more effective as a hair conditioning agent than SB-25. This high level of performance at low concentration levels results in considerably less build-up on the hair and, therefore, less oiliness.
Patent | Priority | Assignee | Title |
10085931, | Mar 09 2012 | L Oreal | Process for protecting and repairing keratin fibres using anionic oxidized polysaccharides |
10159639, | Jun 20 2013 | L Oreal | Composition comprising a combination of an acrylic polymer and an amino silicone |
10772819, | Sep 12 2013 | L Oreal | Process for treating keratin fibres with an oxidised polysaccharide and a sphingosine compound |
10857087, | Sep 12 2013 | L Oreal | Process for treating keratin fibres with a polysaccharide and a pyridinedi-carboxylic acid compound |
10993891, | Dec 19 2014 | L Oreal | Solid anhydrous cosmetic composition, preparation process, cosmetic treatment processes and associated kit |
11000464, | Dec 21 2015 | L Oreal | Dyeing composition at acidic pH comprising a direct dye of triarylmethane structure |
11007131, | Dec 21 2015 | L Oreal | Dyeing composition comprising a direct dye of triarylmethane structure, and a silicone |
11045407, | Sep 12 2013 | L Oreal | Process for treating keratin fibres with a pyridinedicarboxylic acid compound |
11166902, | Jun 20 2013 | L Oreal | Composition comprising a combination of an acrylic polymer, a silicone copolymer and an amino acid or amino acid derivative |
11253459, | May 12 2017 | L Oreal | Dye composition based on copolymers derived from the polymerization of at least one crotonic acid monomer or crotonic acid derivative and of at least one thickening polymer bearing (meth)acrylic acid unit(s), and process for dyeing keratin fibers using same |
11344482, | Sep 28 2017 | L Oreal | Aerosol device for pigment dyeing based on a particular acrylic polymer and a silicone compound, dyeing process |
11382849, | Dec 22 2015 | L Oreal | Non-dyeing composition comprising a cationic acrylic copolymer and a conditioning agent |
11439576, | Mar 12 2018 | Clariant International Ltd | Cosmetic compositions comprising fatty acid esters of oxalkylated alkylalkylene diamines and/or their salts for hair repair treatments |
11510861, | Dec 22 2015 | L Oreal | Hair treatment process using a composition comprising at least one cationic acrylic copolymer |
11612554, | Jul 31 2020 | L Oreal | Hair treatment compositions containing amino acids |
11666521, | Dec 11 2018 | L Oreal | Conditioning compositions containing cationic compounds, a silane compound and silica particles and methods for use |
4325940, | Nov 24 1976 | STEPAN COMPANY, NORTHFIELD, IL 60093 A CORP OF DE | Anti-microbial, cosmetic and water-treating ionene polymeric compounds |
4423032, | Feb 05 1981 | Kao Soap Co., Ltd. | Hair treatments |
4479893, | Oct 28 1981 | Kao Corporation | Shampoo composition containing phosphoric acid ester and organic silicon derivative |
4559227, | Oct 31 1984 | Dow Corning Corporation | Conditioning shampoo containing amine functional polydiorganosiloxane |
4597962, | Jul 01 1983 | L'Oreal | Hair-care composition and hair treatment process |
4601902, | Jul 30 1983 | Dow Corning Limited | Compositions and process for treating hair |
4654161, | May 15 1984 | Goldschmidt AG | Siloxanes with betaine groups, their synthesis and use in cosmetic preparations |
4710314, | Oct 12 1984 | L'Oreal | Detergent cosmetic composition containing a soap and cationic compound |
4749565, | Sep 21 1984 | L'Oreal | Cosmetic compositions based on cationic silicone, water-soluble heteropolysaccharide and electrolyte |
4777037, | Jul 29 1981 | HELENE CURTIS, INC | Hair conditioning compositions containing volatile cyclic silicone and quaternary nitrogen-containing agent |
4820308, | Oct 12 1984 | L'Oreal | Detergent cosmetic compositions containing a soap and cationic compound and direct dye |
4842849, | May 08 1981 | L'Oreal | Composition intended for the treatment of keratin fibres, based on a cationic polymer and an anionic polymer containing vinylsulphonic groups |
4891166, | Jun 06 1987 | Goldschmidt GmbH | Diquaternary polysiloxanes, their synthesis and use in cosmetic preparations |
4902499, | Apr 04 1986 | The Procter & Gamble Company; Procter & Gamble Company, The | Hair care compositions containing a rigid silicone polymer |
4906459, | Oct 23 1987 | The Procter & Gamble Company | Hair care compositions |
4983377, | Oct 31 1989 | Procter & Gamble Company, The | Silicone hairspray compositions |
4983383, | Nov 21 1988 | Procter & Gamble Company, The | Hair care compositions |
5098979, | Mar 25 1991 | SILTECH CORP | Novel silicone quaternary compounds |
5100657, | May 01 1990 | The Procter & Gamble Company; Procter & Gamble Company, The | Clean conditioning compositions for hair |
5104643, | Nov 04 1988 | L'Oreal | Shaving composition for the skin based on polyorgano-siloxanes containing a hydroxyalkyl group and process for use |
5153294, | Mar 25 1991 | SILTECH CORP | Silicone ester quaternary compounds |
5166297, | Mar 25 1991 | SILTECH CORP | Silicone ester quaternary compounds |
5196499, | Jan 21 1992 | SILTECH CORP | Terminal silicone ester quaternary compounds |
5198209, | Feb 11 1992 | Amway Corporation | Conditioning shampoo |
5213793, | Jan 13 1984 | Henkel IP & Holding GmbH | Hair conditioning |
5246607, | Nov 08 1988 | Goldschmidt GmbH | Methylpolysiloxanes with quaternary ammonium groups as corrosion inhibitors for preparations consisting predominantly of water |
5405983, | Dec 28 1993 | Mona Industries, Inc. | Silicone modified phospholipid compositions |
5468477, | May 12 1992 | Minnesota Mining and Manufacturing Company | Vinyl-silicone polymers in cosmetics and personal care products |
5596061, | Dec 28 1993 | Mona Industries, Inc. | Organosilicone having a carboxyl functional group thereon |
5623043, | Dec 28 1993 | Mona Industries, Inc. | Silicone modified phospholipid compositions |
5653968, | Mar 21 1996 | The Proctor & Gamble Company; Procter & Gamble Company, The | Rinse-off hair care compositions |
5653969, | Mar 21 1996 | The Procter & Gamble Company; Procter & Gamble Company, The | Low residue hair care compositions |
5658557, | Aug 07 1989 | The Procter & Gamble Company | Hair care compositions comprising silicone-containing copolymers |
5660819, | Dec 28 1990 | General Electric Company | Cosmetic formulations |
5665337, | Mar 21 1996 | The Procter & Gamble Company; Procter & Gamble Company, The | Low residue hair care compositions using grafted copolymers |
5667771, | Mar 21 1996 | The Procter & Gamble Company; Procter & Gamble Company, The | Rinse-off hair care compositions using grafted copolymers |
5725882, | May 12 1992 | Minnesota Mining and Manufacturing Company | Vinyl-silicone copolymers in cosmetics and personal care products |
5804173, | Sep 04 1996 | Procter & Gamble Company, The | Personal care compositions |
5830447, | Sep 04 1996 | The Procter & Gamble Company; Procter & Gamble Company, The | Personal care compositions |
5863527, | Sep 04 1996 | The Proctor & Gamble Company; Procter & Gamble Company, The | Personal care compositions |
5911979, | Jan 09 1995 | The Procter & Gamble Company | Aqueous hair setting composition containing silicone grafted copolymer |
5916548, | Sep 04 1996 | The Procter & Gamble Company; Procter & Gamble Company, The | Personal care compositions |
5929173, | May 12 1997 | Procter & Gamble Company, The | Toughened grafted polymers |
5997853, | Aug 07 1989 | The Procter & Gamble | Hair conditioning and styling compositions |
6106820, | May 12 1997 | Procter & Gamble Company, The | Cosmetic compositions |
6165457, | May 12 1997 | PROCTER & GAMBLE COMPANY THE | Personal care compositions containing toughened grafted polymers |
6225489, | Dec 28 1993 | Mona Industries, Inc. | Silicone modified phospholipid compositions |
6251145, | Oct 03 1997 | L'Oreal S.A. | Oxidizing composition and uses for dyeing, permanently setting or bleaching keratin fibres |
6254646, | Oct 03 1997 | L'Oreal S.A. | Oxidizing composition and uses for dyeing, permanently setting or bleaching keratin fibres |
6270534, | Oct 03 1997 | L'Oreal S.A. | Oxidizing composition and uses for dyeing, permanently setting or bleaching keratin fibres |
6423305, | Dec 29 1997 | L'Oreal S.A. | Cosmetic composition comprising at least an amidoethercarboxylic acid surfactant and at least a cationic polymer/anionic polymer combination |
6451747, | Jun 07 1996 | L'Oreal S.A. | Detergent cosmetic compositions for hair care and utilisation thereof |
6471953, | Jun 28 1999 | L OREAL S A | Permanent-waving process comprising the preliminary application of a composition comprising at least one anionic polymer |
6555117, | Apr 25 1997 | The Procter & Gamble Company; PROCTOR & GAMBLE COMPANY, THE | Personal care compositions containing linear toughened silicone grafted polymers |
6562324, | May 11 1993 | 3M Innovative Properties Company | Polymers in cosmetics and personal care products |
6565837, | May 22 1996 | Mona Industries, Inc | Organosilicone having a carboxyl functional group thereon |
6808701, | Mar 21 2000 | JOHNSON & JOHNSON CONSUMER INC ; JOHNSON & JOHNSON CONSUMER COMPANIES, LLC | Conditioning compositions |
7141079, | Apr 12 2000 | L OREAL S A | Oxidation dyeing composition for keratinous fibers and dyeing method using same |
7147673, | Apr 01 2003 | L OREAL S A | Composition for dyeing human keratin materials, comprising at least one fluorescent dye and at least one insoluble polyorganosiloxane conditioning polymer, process therefor and use thereof |
7150764, | Apr 01 2003 | L OREAL S A | Composition for dyeing a human keratin material, comprising at least one fluorescent dye and at least one insoluble conditioning agent, process thereof, use thereof, and devices thereof |
7186278, | Apr 01 2003 | L OREAL S A | Composition for dyeing human keratin materials, comprising at least one fluorescent dye and at least one compound comprising an acid functional group and processes therefor |
7192454, | Apr 01 2003 | L OREAL S A | Composition for dyeing human keratin materials, comprising a fluorescent dye and a particular sequestering agent, process therefor and use thereof |
7195650, | Apr 01 2003 | L OREAL S A | Process for dyeing, with a lightening effect, human keratin fibers that have been permanently reshaped, using at least one composition comprising at least one fluorescent dye |
7195651, | Apr 01 2003 | L OREAL S A | Cosmetic composition for dyeing human keratin materials, comprising at least one fluorescent dye and at least one cationic polymer, and a dyeing process therefor |
7198650, | Apr 01 2003 | L OREAL S A | Method of dyeing human keratin materials with a lightening effect with compositions comprising at least one fluorescent dye and at least one amphoteric or nonionic surfactant, composition thereof, process thereof, and device therefor |
7204860, | Apr 01 2003 | L OREAL S A | Composition for dyeing human keratin materials, comprising at least one fluorescent dye and at least one polyol, process therefor and use thereof |
7208018, | Apr 01 2003 | L OREAL S A | Composition for dyeing human keratin materials, comprising at least one fluorescent dye and at least one associative polymer, process therefor and use thereof |
7217296, | Sep 28 2001 | L OREAL S A | Dyeing composition with a lightening effect for human keratin materials comprising at least one fluorescent dye |
7250064, | Apr 01 2003 | L OREAL S A | Dye composition comprising at least one fluorescent dye and a non-associative thickening polymer for human keratin materials, process therefor, and method thereof |
7261744, | Dec 24 2002 | L OREAL S A | Method for dyeing or coloring human keratin materials with lightening effect using a composition comprising at least one fluorescent compound and at least one optical brightener |
7303589, | Apr 01 2003 | L OREAL S A | Process for dyeing human keratin fibers, having a lightening effect, comprising at least one fluorescent compound and compositions of the same |
7374582, | May 02 2006 | L Oreal | Conditioning cream color base having improved color deposition properties |
7507260, | Jul 29 1999 | L'Oreal S.A. | Composition for dyeing keratinous fibres with a cationic direct dye and a silicone |
7514091, | Jul 23 1998 | L OREAL S A | Aminated silicone detergent cosmetic composition and use |
7622512, | Dec 21 2005 | Bausch & Lomb Incorporated | Cationic hydrophilic siloxanyl monomers |
7691917, | Jun 14 2007 | Bausch & Lomb Incorporated | Silcone-containing prepolymers |
7736631, | Apr 01 2003 | L Oreal | Cosmetic dye composition with a lightening effect for human keratin materials, comprising at least one fluorescent dye and at least one aminosilicone, and process of dyeing |
7759408, | Dec 21 2005 | Bausch & Lomb Incorporated | Silicon-containing monomers end-capped with polymerizable cationic hydrophilic groups |
7776989, | Feb 02 2005 | Evonik Degussa GmbH | UV-light-absorbing quaternary polysiloxanes |
7838478, | Aug 09 2002 | Kao Corporation | Hair detergent compositions |
7960447, | Apr 13 2006 | Bausch & Lomb Incorporated | Cationic end-capped siloxane prepolymer for reduced cross-link density |
8013097, | Apr 11 2007 | Dow Corning Corporation | Silicone polyether block copolymers having organofunctional endblocking groups |
8053395, | Jan 19 2007 | Halliburton Energy Services, Inc. | Compositions for increasing gas production from a subterranean formation |
8114389, | Jan 21 2000 | L'Oreal S.A. | Nanoemulsions comprising at least one amphiphilic lipid, at least one oil, and at least one nonionic polymer, and uses thereof |
8163273, | Apr 06 2001 | L OREAL S A | Process for permanently reshaping the hair using aminosilicones |
8246941, | May 24 2005 | L OREAL S A | Detergent cosmetic compositions comprising at least one amino silicone, and use thereof |
8263061, | Jan 22 2009 | Siltech Corporation | Alkyl quaternium silicone compounds |
8302691, | Jan 19 2007 | Halliburton Energy Services, Inc. | Methods for increasing gas production from a subterranean formation |
8545817, | Aug 04 2006 | L OREAL S A | Cosmetic composition comprising at least one polysaccharide of λ-carrageenan type in aerosol form, method for the cosmetic treatment of keratinous fibers, and product comprising the composition |
8802066, | Dec 21 2010 | L Oreal | Cosmetic composition comprising a particular zinc salt and an amino silicone |
8828368, | Dec 21 2010 | L Oreal | Cosmetic composition comprising a particular zinc salt and a starch |
8905049, | Sep 24 2010 | L Oreal | Process for treating keratin fibres using a non-detergent cosmetic composition comprising at least one calcium salt |
9248083, | Dec 23 2009 | L OREAL S A | Cosmetic composition comprising at least one organosilicon compound, at least two anionic surfactants and at least one amphoteric surfactant |
9375393, | Dec 21 2010 | L Oreal | Composition comprising a non-nitrogenous zinc salt and a particular cationic surfactant |
9539190, | May 07 2010 | CONOPCO, INC , D B A UNILEVER | Skin conditioning compositions containing 12-hydroxystearic acid |
9776020, | May 27 2011 | L Oreal | Composition comprising an alkoxysilane and a modified starch, and cosmetic use thereof |
9802339, | Dec 13 2013 | Alcon Inc | Method for making contact lenses |
9919456, | Oct 31 2013 | Alcon Inc | Method for producing ophthalmic lenses |
RE34584, | Nov 09 1984 | The Procter & Gamble Company; PROCTER & GAMBLE COMPANY, THE, | Shampoo compositions |
Patent | Priority | Assignee | Title |
3208911, | |||
3248296, | |||
3389160, | |||
3964500, | Dec 26 1973 | CPPD, INC , A CORP OF IL | Lusterizing shampoo containing a polysiloxane and a hair-bodying agent |
Executed on | Assignor | Assignee | Conveyance | Frame | Reel | Doc |
Dec 28 1977 | Union Carbide Corporation | (assignment on the face of the patent) | / | |||
Jul 08 1993 | OSI, SPECIALTIES, INC | CHASE MANHATTAN BANK N A | SECURITY INTEREST SEE DOCUMENT FOR DETAILS | 006624 | /0803 | |
Jul 09 1993 | UNION CARBIDE CHEMICALS AND PLASTICS CORP | OSI SPECIALTIES, INC | ASSIGNMENT OF ASSIGNORS INTEREST SEE DOCUMENT FOR DETAILS | 006633 | /0206 |
Date | Maintenance Fee Events |
Date | Maintenance Schedule |
Jan 22 1983 | 4 years fee payment window open |
Jul 22 1983 | 6 months grace period start (w surcharge) |
Jan 22 1984 | patent expiry (for year 4) |
Jan 22 1986 | 2 years to revive unintentionally abandoned end. (for year 4) |
Jan 22 1987 | 8 years fee payment window open |
Jul 22 1987 | 6 months grace period start (w surcharge) |
Jan 22 1988 | patent expiry (for year 8) |
Jan 22 1990 | 2 years to revive unintentionally abandoned end. (for year 8) |
Jan 22 1991 | 12 years fee payment window open |
Jul 22 1991 | 6 months grace period start (w surcharge) |
Jan 22 1992 | patent expiry (for year 12) |
Jan 22 1994 | 2 years to revive unintentionally abandoned end. (for year 12) |